Computational study of the synthesis of benzoin derivatives from benzil

Topal K., Unaleroglu C., Aviyente V.

INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, cilt.106, sa.7, ss.1596-1610, 2006 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 106 Sayı: 7
  • Basım Tarihi: 2006
  • Doi Numarası: 10.1002/qua.20879
  • Dergi Adı: INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1596-1610
  • Hacettepe Üniversitesi Adresli: Evet

Özet

Benzil (1,2-diphenylethane-1,2-dione) undergoes cyanide catalyzed condensation with benzaldehyde to yield O-benzoylated benzoin (2-benzoyl-1,2-diphenylethanone). In this study, the experimentally suggested mechanism has been modeled with PM3 and verified with B3LYP. The effect of the substituent on the reaction yield has been rationalized by considering two benzil derivatives; 1,2-bis(2-chlorophenyl)ethane-1,2-dione and 1,2-bis(2-fluorophenyl)ethane-1,2-dione and three benzaldehyde derivatives; o-fluorobenzaldehyde, o-methylbenzaldehyde and 2-pyridinecarboxaldehyde. The effect of the solvent has been modeled by using the isodensity-surface polarizable continuum (IPCM) model. Reactivity descriptors have been used to justify the reactivity differences of the various substituents.